Just some of the things I do/bring (full disclosure – I am just a weekend warrior). Bring chain lube, a few shop rags, a few rags you can dampen with water to clean squished bugs off the windscreen and headlights, small set of basic hand tools, tire repair kit and an air source, cash and motorcycle cover. Not sure if the cover helps but the thought is out of sight, out of mind. I only use the cover when the bike is parked overnight. Worked for me so far but who knows if the cover helped or not.
I also use a Garmin GPS. Kind of fun using Basecamp, along with Google maps/street view, to find the most desolate curvy country routes possible. With the route planned ahead of time I can kick back and enjoy the ride!
Southwest and western Wisconsin is intensely beautiful, especially as you get closer to the Mississippi river and Lacrosse area. There are back roads there where if you use a LOT of imagination it feels like riding through the foothills of the Appalachians. Just keep an eye out for gravel and other debris on the curvy roads. PM sent on the Airhawk seat cushion. Sounds like a great trip, enjoy!